9 Biggest Mistakes Entrepreneurs Make & How to Overcome Them

February 19, 2020

Biggest mistakes entrepreneurs

Making mistakes in business is often regarded as something negative. However, the mistakes entrepreneurs make are just opportunities to learn and grow. Yes, business mistakes can be costly and fatal for a company, but we can confidently say that there never existed an entrepreneur who hasn’t done at least one of the biggest business mistakes.

The important thing about the mistakes entrepreneurs make is to rise above them and not fall in desperation. Drowning in shame and guilt after making serious or even trivial business mistakes is unallowed in entrepreneurship. Moreover, you must deal with the fear of making decisions. Of course, there is always the possibility to make the wrong choice but that shouldn’t scare you. In fact, it should inspire you and make you bolder.

The most common business mistakes entrepreneurs make

Take the number of businesses in the world and multiply it with a million. The number you get is the number of possible business mistakes you can make throughout your entrepreneurial journey. Nevertheless, there are several small business mistakes that almost every entrepreneur has made. 

Play it smart and learn how to avoid the biggest business mistakes before committing them.

Not having professionally drafted contracts

When I started running my business, I undertook various projects after a verbal go ahead – one of the biggest business mistakes I could’ve done if you ask me. I would execute my design and branding work and send off my designs to the clients. When it came to paying my invoice, some clients did not pay

Once they had the work they needed, they did not respond to my demand for payment; emails and telephone calls were ignored. I quickly learnt to have a professionally drafted contract in place and ask for 50% payment upfront and the 50% balance before handing over my files and artwork. These agreements need to be in place to avoid nasty surprises.

Vaishali Shah, Owner of Creative-ID & Ananya Cards

Not spending enough time on your business

As an entrepreneur, it is very easy to get too involved in the day to day operations of your business, getting involved in tasks that are time consuming and not strategically important, which is what I did in the first few years. 

Now 20 years in, knowing that’s one of the worst small business mistakes to make, I work on my business. In other words, I work on the strategy and goals of the business, I prioritise and I delegate where appropriate. I devote more time on my business rather than in my business.

Vaishali Shah

Not having your own niche/path

I spent almost the first 4 years of my business agreeing to everything and marketing to everyone. Ultimately, I ended up taking on cakes that I didn’t like, didn’t charge appropriately for and resented. However, I realised this was one of the worst mistakes entrepreneurs make. 

Hence over the last 12-18 months, I have worked hard on finding my niche, the designs that really make me feel happy. The result has been I am now attracting my ideal clients who love my designs and am becoming known for my particular style. I suppose it was a right of passage but I wish I had found my niche sooner.

Debbie Gillespie, Owner of Debbie Gillespie Cake Design

Not determining what success means to you

I spent far too long listening to podcasts and business coaches who said that money was the indicator of success, so I needed to think about upscaling etc. The pressure led to feeling overwhelmed, loss of creativity and almost sounded the death knell for my business. I had to work out what MY success would look like, not someone else’s.

For me, it was to have a small business that attracted my ideal customers whose requests fulfilled me creatively.  It would allow me a reasonable income but not at the expense of my work-life balance and mental health. I am now happier, more fulfilled in my work and have attracted greater success as my confidence grows. So, I’d say this is one of the biggest mistakes entrepreneurs make.

Debbie Gillespie

Not seeking professional employment advice

In the early days of business, I hired my first member of the team and failed to consider looking into the necessary paperwork and contract in order to protect myself and my business if in the future I needed to make any changes to their position in the company. 

Having learnt the hard way that this was not ideal and caused much stress, I’d say of all the small business mistakes I’ve made this is one of the worst. But the outcome is now I am very vigilant when it comes to entering into partnerships or agreements with anyone and I always have the correct paperwork. If I am unclear in an area that I know needs a contract, I know to consult a legal expert to ask for guidance. 

Bernadette Chapman, Owner of Bernadette Chapman Consultancy

Doubting myself and my abilities

Over the years I have wasted far too much time double guessing myself, doubting my abilities and comparing myself to other business owners. I would say this is mainly due to the significant rise we have seen over the past decade on social media where imposter syndrome really does sneak in

I have worked a lot on my mindset as a result and whilst I still have times where I wobble (what human being doesn’t!), I can now confidently tell myself. “I AM good at what I do, I have nearly two decades of experience, a fantastic reputation, a leader in my field and that I will no longer allow others to make me doubt myself”.

Bernadette Chapman

Thinking I knew it all and not asking for help

In the first 5 years of running my business, I fell into the trap of assuming I knew it all (or if I didn’t know something then the only person who could find the answers was me) – one of the worst small business mistakes I could’ve possibly made . 

Whilst this approach certainly saw me no harm as my business accelerated quite fast after turning the 2nd year in business, I look back now and think I could have avoided wasting a lot of time and preventing myself from much stress if I simply realised that whilst I am a PR expert, I don’t know it all when it comes to running a business and that its ok to ask for help. 

In the last few years I can now recognise when it’s more effective to outsource or get an expert into the business to help me, whether that’s for social media, accountancy, human resources etc. Just because you run your own business, you shouldn’t feel you are expected to know it all, it’s ok to admit your weaknesses and get help in those areas. 

Nicola Russill-Roy, Founder of Propose PR

Not being a good communicator

I am a self confessed control freak, so it has taken me a while to learn that I cannot do it all, I need to delegate in my business in order to grow. But with delegation comes the need to be able to communicate with those you are delegating to, what you expect, what you need doing and when you need it done by. So I found for a while that the tasks being completed by those I was delegating to were not being completed in a way I had hoped. 

After a bit of reflection and looking back at situations, I can see it wasn’t necessarily anyone’s fault, it was more the fact I hadn’t communicated exactly what my expectations were. I am excellent at communicating to my clients but when it came to communicating to my team, I noticed the ‘niggles’ were actually due to my inability to accurately communicate. 

Having worked on this with a consultant, I can see that actually the fear of not being in control was affecting my communication skills! If you need to communicate tasks with your team members, make sure you really are asking them what you truly are expecting in return!

Nicola Russill-Roy

Not creating a brand from the start and merely setting up a business.

I believe there is a big difference between ‘creating a brand’ and ‘setting up a business’ – the latter is what I did initially and saw me attracting the wrong client. When I set up I merely set up a blog, a company name and documented my floristry work. I didn’t give too much thought to a brand, a sustainable business model or narrow down exactly who my ideal client was. As a result, early on I was attracting the wrong sort of clients. 

I re-branded a couple of years later and this is when my business truly elevated and I now get work from my dream ideal clients and I am getting the recognition I know I deserve and that I had hoped to achieve. My lesson learnt is to not rush into setting up a business, it’s not just about coming up with a cool business name, throwing up a website and randomly posting content and hoping for the best.

Emma Soulsby, Owner of Emma Soulsby Flowers


There’ll always be mistakes entrepreneurs make and that’s not the end of the world. What matters is to recognise these business mistakes and minimise damage. Furthermore, small business mistakes are crucial to developing important leadership skills that will later help you upscale your business.

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